(E)-p-methoxycinnamyl (E)-5-phenylpent-2-en-4-yn-1-yl ether | 1363131-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-p-methoxycinnamyl (E)-5-phenylpent-2-en-4-yn-1-yl ether
• 英文别名: 1-methoxy-4-[(E)-3-[(E)-5-phenylpent-2-en-4-ynoxy]prop-1-enyl]benzene
• CAS: 1363131-06-9
• 化学式: C₂₁H₂₀O₂
• 分子量: 304.389
• InChiKey: CKKDTRGNBUFUJY-SVCVZBQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-p-methoxycinnamyl (E)-5-phenylpent-2-en-4-yn-1-yl ether 在 Ru(bpz)₃(PF₆)₂ 、 氧气 作用下， 以 硝基甲烷 为溶剂， 5.0 ℃ 、413.69 kPa 条件下， 反应 2.0h， 生成 、
  参考文献：
  名称：

  Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions

  摘要：

  Structurally novel endoperoxides can be sythesized by the photocatalytic cyclotrimerization of bis(styrene) substrates with molecular oxygen. The optimal catalyst for this process is Ru(bpz)(3)(2+), which is a markedly more efficient catalyst for these photooxygention reactions than conventional organic photosensitizers. The 1,2-dioxolane products are amenable to synthetic manipulation and can be easily processed to 1,4-diols and gamma-hydroxyketones. An initial screen of the biological activity of these compounds reveals promising inhibition of cancer cell growth.

  DOI：

  10.1021/ol300428q
• 作为产物：
  描述：

  (E)-5-phenyl-penta-2-ene-4-yne-1-ol 、 (E)-4-methoxycinnamyl bromide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(E)-p-methoxycinnamyl (E)-5-phenylpent-2-en-4-yn-1-yl ether
  参考文献：
  名称：

  Endoperoxide Synthesis by Photocatalytic Aerobic [2 + 2 + 2] Cycloadditions

  摘要：

  Structurally novel endoperoxides can be sythesized by the photocatalytic cyclotrimerization of bis(styrene) substrates with molecular oxygen. The optimal catalyst for this process is Ru(bpz)(3)(2+), which is a markedly more efficient catalyst for these photooxygention reactions than conventional organic photosensitizers. The 1,2-dioxolane products are amenable to synthetic manipulation and can be easily processed to 1,4-diols and gamma-hydroxyketones. An initial screen of the biological activity of these compounds reveals promising inhibition of cancer cell growth.

  DOI：

  10.1021/ol300428q